Tris(furan-2-yl)phosphane → 2-(5-Benzylbenzofuran-2-yl)pyrimidine-5-carbaldehyde

HRID 2075270Notes

Reaction equation

O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[CH2:17]([C:24]1[CH:25]=[CH:26][C:27]2[O:31][C:30](B(O)O)=[CH:29][C:28]=2[CH:35]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CS[C:38]1[N:43]=[CH:42][C:41]([CH:44]=[O:45])=[CH:40][N:39]=1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=C(C([O-])=O)SC=1.[Cu+]>[CH2:17]([C:24]1[CH:25]=[CH:26][C:27]2[O:31][C:30]([C:38]3[N:43]=[CH:42][C:41]([CH:44]=[O:45])=[CH:40][N:39]=3)=[CH:29][C:28]=2[CH:35]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A 25 mm tube was charged with trifuran-2-ylphosphine (0.0737 g, 0.317 mmol), Pd2 dba3 (0.0411 g, 0.0397 mmol), 5-benzylbenzofuran-2-ylboronic acid (0.500 g, 1.98 mmol), CuTC (0.492 g, 2.58 mmol), 2-(methylthio)pyrimidine-5-carbaldehyde (0.306 g, 1.98 mmol) under argon. The reactants were diluted in 8 mL THF, sealed, and heated to 50° C. overnight. The mixture was filtered through Celite rinsing with 200 mL EtOAc. The green solution was concentrated and adsorbed onto 5 g silica gel, and purified by ISCO, 0-20% EtOAc/hexanes to give 2-(5-benzylbenzofuran-2-yl)pyrimidine-5-carbaldehyde as a light yellow solid. MS (ESI) m/z: Calculated: 314.1; Observed: 315.1 (M++1).

Workup

customsealed
filtrationThe mixture was filtered through Celite
washrinsing with 200 mL EtOAc
concentrationThe green solution was concentrated
custompurified by ISCO, 0-20% EtOAc/hexanes

Sources & evidence

ORD record: ord-c3bb2b5b7d354b9cb0af2ce60c1c7c0e
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919519B2

Reaction notes

Loading…